Trifluoromethyl-thiophene carboxylic acid aniledes and use thereof as fungicides

ABSTRACT

The invention relates to novel biphenyl carboxamides of formula (I), wherein A, R, Z, X, Y, m and n have the meanings given in the description, to multiple methods for producing these substances, to their use for combating unwanted micro-organisms and to novel intermediate products and the production thereof.

The present invention relates to trifluoromethylthiophenecarboxanilides of the general formulae I, II and III

in which the substituents are as defined below:

-   R¹, R⁴ independently of one another are C₁-C₄-alkyl,     C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy (it     being possible for these groups to be substituted by halogen), H,     halogen, nitro, CN; -   R² is H, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy (it being     possible for these groups to be substituted by halogen); -   R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl,     C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl, C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl     (it being possible for these groups to be substituted by R⁷);     phenyl, phenyl-C₁-C₆-alkyl, phenyl-C₂-C₆-alkenyl,     phenyl-C₂-C₆-alkynyl, phenyloxy-C₁-C₆-alkyl,     phenyloxy-C₂-C₆-alkenyl, phenyloxy-C₂-C₆-alkynyl, where the alkyl,     alkenyl and alkynyl moiety may be substituted by R⁷ and the phenyl     ring may be substituted by R⁵; —C(R⁸)═NOR⁶; -   X is O, S or a direct bond; -   R⁵ is H, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₂-C₄-alkenyl,     C₂-C₄-alkynyl (it being possible for these groups to be substituted     by halogen), halogen, nitro, CN, phenyl (which may be substituted by     R¹), phenoxy (which may be substituted by R¹), C₁-C₆-alkylphenyl,     where the alkyl moiety may be substituted by halogen and the phenyl     ring may be substituted by R¹; -   R⁶ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl     (it being possible for these groups to be substituted by halogen),     phenyl, which may be substituted by R¹; -   R⁷ is C₁-C₄-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₂-C₈-alkynyloxy,     C₁-C₄-alkoxy-C₁-C₈-alkoxy (it being possible for these groups to be     substituted by halogen), halogen; -   R⁸ is H, R⁷ or C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl,     C₅-C₁₂-cycloalkenyl, C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl (it being     possible for these groups to be substituted by halogen); phenyl,     which may be substituted by R⁵; -   n is 0-4; -   m is 0, 1.

Furthermore, the present invention relates to the use of the trifluoromethylthiophene-carboxanilides as fungicides, and to compositions comprising them.

EP-A 0545099 discloses acid anilide derivatives and their use for controlling Botrytis. Thiophenecarboxanilides are not described in this application.

Thiophenecarboxanilide derivatives are known from JP 08092223, JP 092592, JP 092593, JP 01302605, JP 01313402, EP-A 915868 and WO 02/08197.

However, the thiophenecarboxanilide derivatives having fungicidal activity that have been described are, in particular at low application rates, not entirely satisfactory.

It is an object of the present invention to provide novel thiophenecarboxanilide derivatives having improved action, and in particular also at low application rates.

We have found that this object is achieved, surprisingly, by the trifluoromethyl-thiophenecarboxanilides of the formulae I, II and III mentioned above.

The organic moieties mentioned in the definition of the substituents R¹ to R⁸ are—like the term halogen—collective terms for individual enumerations of the individual members. All carbon chains, i.e. all alkyl, haloalkyl, arylalkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl moieties, can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen denotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl and the C₁-C₄-alkyl moieties in C₁-C₄-alkoxy: CH₃,         C₂H₅, CH₂—C₂H₅, CH(CH₃)₂, n-butyl, CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ or         C(CH₃)₃;     -   C₁-C₄-haloalkyl and the C₁-C₄-haloalkyl moieties in         C₁-C₄-haloalkoxy: a C₁-C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, CH₂F, CHF₂, CF₃, CH₂Cl,         CH(Cl)₂, C(Cl)₃, chlorofluoromethyl, dichlorofluoromethyl,         chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl,         2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,         2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, C₂F₅, 2-fluoropropyl, 3-fluoropropyl,         2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,         3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,         3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,         CH₂—C₂F₅, CF₂—C₂F₅, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;     -   C₁-C₁₂-alkyl and the C₁-C₈-alkyl moieties in C₁-C₈-alkoxy: a         C₁-C₄-alkyl radical as mentioned above or, for example,         n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,         2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl,         1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,         3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,         1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,         2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,         2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,         1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably         CH₃, C₂H₅, CH₂-C₂H₅, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl,         n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl or         n-dodecyl;     -   C₁-C₁₂-haloalkyl and the C₁-C₈-haloalkyl moieties in         C₁-C₈-haloalkoxy: a C₁-C₁₂-alkyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, one of the radicals         mentioned under C₁-C₄-haloalkyl or 5-fluoro-1-pentyl,         5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl,         5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl,         6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl,         6,6,6-trichloro-1-hexyl or dodecafluorohexyl;     -   C₂-C₄-alkenyl: unsaturated straight-chain or branched         hydrocarbon radicals having 2 to 4 carbon atoms and a double         bond in any position, for example ethenyl, 1-propenyl,         2-propenyl, 1-methylethenyl, 1-buten-1-yl, 1-buten-2-yl,         1-buten-3-yl, 2-buten-1-yl, 1-methylprop-1-en-1-yl,         2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl,         2-methylprop-2-en-1-yl;     -   C₂-C₁₂-alkenyl and the C₂-C₈-alkenyl moieties in         C₂-C₈-alkenyloxy: C₂-C₄-alkenyl and also n-penten-1-yl,         n-penten-2-yl, n-penten-3-yl, n-penten-4-yl,         1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,         3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl,         2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,         1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,         3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,         1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,         1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl,         n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl,         n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl,         3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,         1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,         3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,         1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,         3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,         1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,         3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,         1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,         1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,         1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,         1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,         2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,         2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,         3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,         1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,         1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl,         2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,         1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,         1-ethyl-2-methylprop-1-en-1-yl or         1-ethyl-2-methylprop-2-en-1-yl;     -   C₂-C₄-haloalkenyl: unsaturated straight-chain or branched         hydrocarbon radicals having 2 to 4 carbon atoms and a double         bond in any position (as mentioned above), where in these groups         some or all of the hydrogen atoms are replaced by halogen atoms         as mentioned above, in particular by fluorine, chlorine and         bromine, i.e., for example, 2-chloroallyl, 3-chloroallyl,         2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl,         2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl,         2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoalkyl or         2,3-dibromobut-2-enyl;     -   C₂-C₁₂-haloalkenyl and the haloalkenyl moieties of         C₂-C₈-haloalkenyloxy: C₂-C₁₂-alkenyl as mentioned above which is         partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, for example the radicals mentioned under         C₂-C₄-haloalkenyl;     -   C₂-C₄-alkynyl: straight-chain or branched hydrocarbon groups         having 2 to 4 carbon atoms and a triple bond in any position,         for example ethynyl, 1-propynyl, 2-propynyl (=propargyl),         1-butynyl, 2-butynyl, 3-butynyl and 1-methyl-2-propynyl;     -   C₂-C₁₂-alkynyl and the C₂-C₈-alkynyl moieties in         C₂-C₈-alkynyloxy: straight-chain or branched hydrocarbon groups         having 2 to 12 carbon atoms and a triple bond in any position,         for example ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl,         n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl,         n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl,         n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,         n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,         3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,         n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl,         n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl,         n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl,         3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,         3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl,         4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and         4-methylpent-2-yn-5-yl, preferably prop-2-yn-1-yl;     -   C₂-C₄-haloalkynyl: unsaturated straight-chain or branched         hydrocarbon radicals having 2 to 4 carbon atoms and a triple         bond in any position (as mentioned above), where in these groups         some or all of the hydrogen atoms may be replaced by halogen         atoms as mentioned above, in particular by fluorine, chlorine         and bromine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl,         4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,         1,1-difluorobut-2-yn-1-yl, 5-fluoropent-3-yn-1-yl or         6-fluorohex-4-yn-1-yl;     -   C₂-C₁₂-haloalkynyl and the C₂-C₈-haloalkynyl moieties in         C₂-C₈-haloalkynyloxy: C₂-C₁₂-alkynyl as mentioned above which is         partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, for example the radicals mentioned under         C₂-C₄-haloalkynyl;     -   C₁-C₄-alkoxy: OCH₃, OC₂H₅, OCH₂—C₂H₅, OCH(CH₃)₂, n-butoxy,         OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂ or C(CH₃)₃, preferably OCH₃, OC₂H₅         or OCH(CH₃)₂;     -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, OCH₂F, OCHF₂, OCF₃,         OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, chlorofluoromethoxy,         dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,         2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, OC₂F₅, 2-fluoropropoxy, 3-fluoropropoxy,         2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy,         3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,         3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy,         1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or         nonafluorobutoxy, preferably OCHF₂, OCF₃, dichlorofluoromethoxy,         chlorodifluoromethoxy or 2,2,2-trifluoroethoxy;     -   C₁-C₈-alkoxy: a C₁-C₄-alkoxy radical as mentioned above or, for         example, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy,         3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy,         1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy,         2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,         1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,         2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,         1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,         1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or         1-ethyl-2-methylpropoxy, preferably OCH₃, OC₂H₅, OCH₂—C₂H₅,         OCH(CH₃)₂, n-butoxy, OC(CH₃)₃, n-pentoxy or n-hexoxy;     -   C₁-C₈-haloalkoxy: a C₁-C₈-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, one of the radicals         mentioned under C₁-C₄-haloalkoxy or 5-fluoro-1-pentoxy,         5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy,         5,5,5-trichloro-1-pentoxy, undecafluoropentoxy,         6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy,         6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy;     -   C₃-C₁₂-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl,         cyclohexyl, cycloheptyl or cyclooctyl;     -   C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted         by C₃-C₁₂-cycloalkyl, for example cyclopropylmethyl,         cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,         cycloheptylmethyl, cyclooctylmethyl, 2-(cyclopropyl)ethyl,         2-(cyclobutyl)ethyl, 2-(cyclopentyl)ethyl, 2-(cyclohexyl)ethyl,         2-(cycloheptyl)ethyl, 2-(cyclooctyl)ethyl,         3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl,         3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl,         3-(cycloheptyl)propyl, 3-(cyclooctyl)propyl,         4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl, 4-(cyclopentyl)butyl,         4-(cyclohexyl)butyl, 4-(cycloheptyl)butyl, 4-(cyclooctyl)butyl;     -   phenyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by phenyl,         for example benzyl, 1- or 2-phenylethyl, 1-, 2- or         3-phenylpropyl;     -   phenyloxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by         phenoxy, for example phenoxymethyl, 1- or 2-phenoxyethyl, 1-, 2-         or 3-phenoxypropyl;     -   phenyl-C₂-C₆-alkenyl: C₂-C₆-alkenyl which is substituted by         phenyl, for example 1- or 2-phenylethenyl,         1-phenylprop-2-en-1-yl, 3-phenylprop-1-en-1-yl,         3-phenylprop-2-en-1-yl, 4-phenylbut-1-en-1-yl or         4-phenylbut-2-en-1-yl;     -   phenyl-C₂-C₆-alkynyl: C₂-C₆-alkynyl which is substituted by         phenyl, for example 1-phenylprop-2-yn-1-yl,         3-phenylprop-1-yn-1-yl, 3-phenylprop-2-yn-1-yl,         4-phenylbut-1-yn-1-yl or 4-phenylbut-2-yn-1-yl.

Preference is given to trifluoromethylthiophenecarboxanilides of the formulae I, II and III in which the substituents are as defined below:

-   R¹ is halogen or C₁-C₄-alkyl, which may be substituted by halogen,     is particularly preferably fluorine, chlorine, bromine or methyl; -   R² is H, methyl, OH or methoxy; -   R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl,     C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl, it being possible for these     groups to be substituted by halogen and C₁-C₄-alkyl; phenyl,     phenyl-C₁-C₆-alkyl, it being possible for the phenyl ring to be     substituted by R⁵; or —C(C₁-C₄-alkyl)=NO—R⁶, it being possible for     the C₁-C₄-alkyl group to be substituted by halogen; -   X is a direct bond or O, is particularly preferably a direct bond,     is furthermore particularly preferably O; -   R⁴ is halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy (it being possible for     these groups to be substituted by halogen), is particularly     preferably fluorine, chlorine, methyl, trifluoromethyl or methoxy,     trifluoromethoxy, difluoromethyl; -   R⁵ is H, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₂-C₄-alkenyl,     C₂-C₄-alkynyl (it being possible for these groups to be substituted     by halogen), halogen, nitro, CN, phenyl (which may be substituted by     R¹), phenoxy (which may be substituted by R¹), C₁-C₆-alkylphenyl,     where the alkyl moiety may be substituted by halogen and the phenyl     ring may be substituted by R¹; -   R⁶ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl     (it being possible for these groups to be substituted by halogen),     -   phenyl which may be substituted by R¹; -   R⁷ is C₁-C₄-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₂-C₈-alkynyloxy,     C₁-C₄-alkoxy-C₁-C₈-alkoxy (it being possible for these groups to be     substituted by halogen), halogen; -   R⁸ is H, R⁷ or C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl,     C₅-C₁₂-cycloalkenyl, C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl (it being     possible for these groups to be substituted by halogen);     -   phenyl, which may be substituted by R⁵; -   n is 0-4, preferably 0 or 1, particularly preferably 0; -   m is 0 or 1, particularly preferably 0.

Particular preference is given to trifluoromethylthiophenecarboxanilides of the formulae Ia, Ib, IIa, lIb, IIIa and IIIb

in which the substituents are as defined below:

-   R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl,     C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl,     -   it being possible for these groups to be substituted by halogen         or C₁-C₄-alkyl; phenyl, phenyl-C₁-C₆-alkyl, it being possible         for the phenyl ring to be substituted by R⁵, or     -   —C(C₁-C₄-alkyl)=NO—R⁶, it being possible for the C₁-C₄-alkyl         group to be substituted by halogen; -   X is a direct bond or O, particularly preferably a direct bond,     furthermore particularly preferably O.

With a view to their use as fungicides and active compounds for controlling pests, particular preference is given to the individual compounds compiled in tables 1 to 120 below, which are embraced by the formulae Ia, Ib, Ic, Id, IIa, IIb, IIc, IId, IIIa, IIIb, IIIc and IIId.

TABLE A No. R³ 1 CH₃ 2 C₂H₅ 3 n-C₃H₇ 4 i-C₃H₇ 5 cyclopropyl 6 n-C₄H₉ 7 s-C₄H₉ 8 i-C₄H₉ 9 t-C₄H₉ 10 n-C₅H₁₁ 11 i-C₅H₁₁ 12 neo-C₅H₁₁ 13 cyclopentyl 14 n-C₆H₁₃ 15 cyclohexyl 16 cyclobutyl 17 CH₂CH₂Cl 18 (CH₂)₄Cl 19 2-methoxyeth-1-yl 20 2-ethoxyeth-1-yl 21 2-isopropoxyeth-1-yl 22 2-vinyloxyeth-1-yl 23 allyloxyeth-1-yl 24 2-trifluoromethoxyeth-1-yl 25 prop-2-yn-1-yl 26 but-2-yn-1-yl 27 but-3-yn-1-yl 28 3-chloroprop-2-yn-1-yl 29 benzyl 30 1-naphthyl-CH₂ 31 2-naphthyl-CH₂ 32 2-phenoxyeth-1-yl 33 2-(2′-chlorophenoxy)eth-1-yl 34 2-(3′-chlorophenoxy)eth-1-yl 35 2-(4′-chlorophenoxy)eth-1-yl 36 2-(3′,5′-dichlorophenoxy)eth-1-yl 37 2-(2′-cyanophenoxy)eth-1-yl 38 2-(3′-cyanophenoxy)eth-1-yl 39 2-(4′-cyanophenoxy)eth-1-yl 40 2-(2′-methylphenoxy)eth-1-yl 41 2-(3′-methylphenoxy)eth-1-yl 42 2-(4′-methylphenoxy)eth-1-yl 43 2-(3′-t-butylphenoxy)eth-1-yl 44 2-(4′-t-butylphenoxy)eth-1-yl 45 2-(2′-nitrophenoxy)eth-1-yl 46 2-(3′-nitrophenoxy)eth-1-yl 47 2-(4′-nitrophenoxy)eth-1-yl 48 2-(2′-methoxyphenoxy)eth-1-yl 49 2-(3′-methoxyphenoxy)eth-1-yl 50 2-(4′-methoxyphenoxy)eth-1-yl 51 2-(2′-trifluoromethylphenoxy)eth-1-yl 52 2-(3′-trifluoromethylphenoxy)eth-1-yl 53 2-(4′-trifluoromethylphenoxy)eth-1-yl 54 2-phenyleth-1-yl 55 2-(2′-chlorophenyl)eth-1-yl 56 2-(3′-chlorophenyl)eth-1-yl 57 2-(4′-chlorophenyl)eth-1-yl 58 2-(3′,5′-dichlorophenyl)eth-1-yl 59 2-(2′-cyanophenyl)eth-1-yl 60 2-(3′-cyanophenyl)eth-1-yl 61 2-(4′-cyanophenyl)eth-1-yl 62 2-(2′-methylphenyl)eth-1-yl 63 2-(3′-methylphenyl)eth-1-yl 64 2-(4′-methylphenyl)eth-1-yl 65 2-(2′-methoxyphenyl)eth-1-yl 66 2-(3′-methoxyphenyl)eth-1-yl 67 2-(4′-methoxyphenyl)eth-1-yl 68 2-(2′-trifluoromethylphenyl)eth-1-yl 69 2-(3′-trifluoromethylphenyl)eth-1-yl 70 2-(4′-trifluoromethylphenyl)eth-1-yl 71 C₆H₅ 72 2-F—C₆H₄ 73 3-F—C₆H₄ 74 4-F—C₆H₄ 75 2,3-F₂—C₆H₃ 76 2,4-F₂—C₆H₃ 77 2,5-F₂—C₆H₃ 78 2,6-F₂—C₆H₃ 79 3,4-F₂—C₆H₃ 80 3,5-F₂—C₆H₃ 81 2-Cl—C₆H₄ 82 3-Cl—C₆H₄ 83 4-Cl—C₆H₄ 84 2,3-Cl₂—C₆H₃ 85 2,4-Cl₂—C₆H₃ 86 2,5-Cl₂—C₆H₃ 87 2,6-Cl₂—C₆H₃ 88 3,4-Cl₂—C₆H₃ 89 3,5-Cl₂—C₆H₃ 90 2,3,4-Cl₃—C₆H₂ 91 2,3,5-Cl₃—C₆H₂ 92 2,3,6-Cl₃—C₆H₂ 93 2,4,5-Cl₃—C₆H₂ 94 2,4,6-Cl₃—C₆H₂ 95 3,4,5-Cl₃—C₆H₂ 96 2-Br—C₆H₄ 97 3-Br—C₆H₄ 98 4-Br—C₆H₄ 99 2,3-Br₂—C₆H₃ 100 2,4-Br₂—C₆H₃ 101 2,5-Br₂—C₆H₃ 102 2,6-Br₂—C₆H₃ 103 3,4-Br₂—C₆H₃ 104 3,5-Br₂—C₆H₃ 105 2-F, 3-Cl—C₆H₃ 106 2-F, 4-Cl—C₆H₃ 107 2-F, 5-Cl—C₆H₃ 108 2-F, 3-Br—C₆H₃ 109 2-F, 4-Br—C₆H₃ 110 2-F, 5-Br—C₆H₃ 111 2-Cl, 3-Br—C₆H₃ 112 2-Cl, 4-Br—C₆H₃ 113 2-Cl, 5-Br—C₆H₃ 114 3-F, 4-Cl—C₆H₃ 115 3-F, 5-Cl—C₆H₃ 116 3-F, 6-Cl—C₆H₃ 117 3-F, 4-Br—C₆H₃ 118 3-F, 5-Br—C₆H₃ 119 3-F, 6-Br—C₆H₃ 120 3-Cl, 4-Br—C₆H₃ 121 3-Cl, 5-Br—C₆H₃ 122 3-Cl, 6-Br—C₆H₃ 123 4-F, 5-Cl—C₆H₃ 124 4-F, 6-Cl—C₆H₃ 125 4-F, 5-Br—C₆H₃ 126 4-F, 6-Br—C₆H₃ 127 4-Cl, 5-Br—C₆H₃ 128 5-F, 6-Cl—C₆H₃ 129 5-F, 6-Br—C₆H₃ 130 5-Cl, 6-Br—C₆H₃ 131 3-Br, 4-Cl, 5-Br—C₆H₂ 132 2-CN—C₆H₄ 133 3-CN—C₆H₄ 134 4-CN—C₆H₄ 135 2-NO₂—C₆H₄ 136 3-NO₂—C₆H₄ 137 4-NO₂—C₆H₄ 138 2-CH₃—C₆H₄ 139 3-CH₃—C₆H₄ 140 4-CH₃—C₆H₄ 141 2,3-(CH₃)₂—C₆H₃ 142 2,4-(CH₃)₂—C₆H₃ 143 2,5-(CH₃)₂—C₆H₃ 144 2,6-(CH₃)₂—C₆H₃ 145 3,4-(CH₃)₂—C₆H₃ 146 3,5-(CH₃)₂—C₆H₃ 147 2-C₂H₅—C₆H₄ 148 3-C₂H₅—C₆H₄ 149 4-C₂H₅—C₆H₄ 150 2-i-C₃H₇—C₆H₄ 151 3-i-C₃H₇—C₆H₄ 152 4-i-C₃H₇—C₆H₄ 153 3-tert-C₄H₉—C₆H₄ 154 4-tert-C₄H₉—C₆H₄ 155 2-vinyl-C₆H₄ 156 3-vinyl-C₆H₄ 157 4-vinyl-C₆H₄ 158 2-allyl-C₆H₄ 159 3-allyl-C₆H₄ 160 4-allyl-C₆H₄ 161 2-C₆H₅—C₆H₄ 162 3-C₆H₅—C₆H₄ 163 4-C₆H₅—C₆H₄ 164 3-CH₃, 5-tert-C₄H₉—C₆H₃ 165 2-OH—C₆H₄ 166 3-OH—C₆H₄ 167 4-OH—C₆H₄ 168 2-OCH₃—C₆H₄ 169 3-OCH₃—C₆H₄ 170 4-OCH₃—C₆H₄ 171 2,3-(OCH₃)₂—C₆H₃ 172 2,4-(OCH₃)₂—C₆H₃ 173 2,5-(OCH₃)₂—C₆H₃ 174 3,4-(OCH₃)₂—C₆H₃ 175 3,5-(OCH₃)₂—C₆H₃ 176 3,4,5-(OCH₃)₃—C₆H₂ 177 2-OC₂H₅—C₆H₄ 178 3-OC₂H₅—C₆H₄ 179 4-OC₂H₅—C₆H₄ 180 2-O-(n-C₃H₇)—C₆H₄ 181 3-O-(n-C₃H₇)—C₆H₄ 182 4-O-(n-C₃H₇)—C₆H₄ 183 2-O-(i-C₃H₇)—C₆H₄ 184 3-O-(i-C₃H₇)—C₆H₄ 185 4-O-(i-C₃H₇)—C₆H₄ 186 4-O-(n-C₄H₉)—C₆H₄ 187 3-O-(t-C₄H₉)—C₆H₄ 188 4-O-(t-C₄H₉)—C₆H₄ 189 2-O-allyl-C₆H₄ 190 3-O-allyl-C₆H₄ 191 4-O-allyl-C₆H₄ 192 2-CF₃—C₆H₄ 193 3-CF₃—C₆H₄ 194 4-CF₃—C₆H₄ 195 2-acetyl-C₆H₄ 196 3-acetyl-C₆H₄ 197 4-acetyl-C₆H₄ 198 2-methoxycarbonyl-C₆H₄ 199 3-methoxycarbonyl-C₆H₄ 200 4-methoxycarbonyl-C₆H₄ 201 2-aminocarbonyl-C₆H₄ 202 3-aminocarbonyl-C₆H₄ 203 4-aminocarbonyl-C₆H₄ 204 2-dimethylaminocarbonyl-C₆H₄ 205 3-dimethylaminocarbonyl-C₆H₄ 206 4-dimethylaminocarbonyl-C₆H₄ 207 2-(N-methylaminocarbonyl)-C₆H₄ 208 3-(N-methylaminocarbonyl)-C₆H₄ 209 4-(N-methylaminocarbonyl)-C₆H₄ 210 2-H₂N—C₆H₄ 211 3-H₂N—C₆H₄ 212 4-H₂N—C₆H₄ 213 2-aminothiocarbonyl-C₆H₄ 214 3-aminothiocarbonyl-C₆H₄ 215 4-aminothiocarbonyl-C₆H₄ 216 2-methoxyiminomethyl-C₆H₄ 217 3-methoxyiminomethyl-C₆H₄ 218 4-methoxyiminomethyl-C₆H₄ 219 3,4-methylenedioxy-C₆H₃ 220 3,4-difluoromethylenedioxy-C₆H₃ 221 2,3-methylenedioxy-C₆H₃ 222 2-(1′-methoxyiminoeth-1′-yl)-C₆H₄ 223 3-(1′-methoxyiminoeth-1′-yl)-C₆H₄ 224 4-(1′-methoxyiminoeth-1′-yl)-C₆H₄ 225 2-SCH₃—C₆H₄ 226 3-SCH₃—C₆H₄ 227 4-SCH₃—C₆H₄ 228 2-SO₂CH₃—C₆H₄ 229 3-SO₂CH₃—C₆H₄ 230 4-SO₂CH₃—C₆H₄ 231 2-OCF₃—C₆H₄ 232 3-OCF₃—C₆H₄ 233 4-OCF₃—C₆H₄ 234 2-OCHF₂—C₆H₄ 235 3-OCHF₂—C₆H₄ 236 4-OCHF₂—C₆H₄ 237 3-CF₃, 4-OCF₃—C₆H₃ 238 2-NHCH₃—C₆H₄ 239 3-NHCH₃—C₆H₄ 240 4-NHCH₃—C₆H₄ 241 2-N(CH₃)₂—C₆H₄ 242 3-N(CH₃)₂—C₆H₄ 243 4-N(CH₃)₂—C₆H₄ 244 2-ethoxycarbonyl-C₆H₄ 245 3-ethoxycarbonyl-C₆H₄ 246 4-ethoxycarbonyl-C₆H₄ 247 2-CH₂CH₂F—C₆H₄ 248 3-CH₂CH₂F—C₆H₄ 249 4-CH₂CH₂F—C₆H₄ 250 2-CH₂CF₃—C₆H₄ 251 3-CH₂CF₃—C₆H₄ 252 4-CH₂CF₃—C₆H₄ 253 2-CF₂CHF₂—C₆H₄ 254 3-CF₂CHF₂—C₆H₄ 255 4-CF₂CHF₂—C₆H₄ 256 2-CHF₂—C₆H₄ 257 3-CHF₂—C₆H₄ 258 4-CHF₂—C₆H₄ 259 2-(1′-oxo-n-prop-1-yl)-C₆H₄ 260 3-(1′-oxo-n-prop-1-yl)-C₆H₄ 261 4-(1′-oxo-n-prop-1-yl)-C₆H₄ 262 2-(1′-oxoisoprop-1-yl)-C₆H₄ 263 3-(1′-oxoisoprop-1-yl)-C₆H₄ 264 4-(1′-oxoisoprop-1-yl)-C₆H₄ 265 3-cyclopropyl-C₆H₄ 266 4-cyclopropyl-C₆H₄ 267 4-cyclohexyl-C₆H₄ 268 —C≡CH 269 —C≡C—Cl 270 —C≡C—Br 271 —C≡C—CH₃ 273 —C≡C—C₆H₅ 274 —C≡C-[2-Cl—C₆H₄] 275 —C≡C-[4-Cl—C₆H₄] 276 —C≡C-[2,4-Cl₂—C₆H₃] 277 —C≡C-[2-CH₃—C₆H₄] 278 —C≡C-[4-CH₃—C₆H₄] 279 —C≡C-[2,4-(CH₃)₂—C₆H₃] 280 —C≡C-[2-Cl, 4-CH₃—C₆H₃] 281 —C≡C-[2-CH₃, 4-Cl—C₆H₃] 282 —C≡C-[3-CF₃—C₆H₄] 283 —C≡C-[3-Cl, 5-CF₃—C₆H₃] 284 —C≡C-[2-OCH₃—C₆H₄] 285 —C≡C-[4-OCH₃—C₆H₄] 286 —C≡C-[2,4-(OCH₃)₂—C₆H₃] 287 —C≡C-[2-Cl, 4-OCH₃—C₆H₃] 288 —C≡C-[2-OCH₃, 4-Cl—C₆H₃] 289 —C≡C-[3-OCHF₂—C₆H₄] 290 —C≡C-[3-Cl, 5-OCHF₂—C₆H₃] 291 cyclopentyl 292 1-CH₃-cyclopentyl 293 2-CH₃-cyclopentyl 294 3-CH₃-cyclopentyl 295 2,3-(CH₃)₂-cyclopentyl 296 1-Cl-cyclopentyl 297 2-Cl-cyclopentyl 298 3-Cl-cyclopentyl 299 2-CH₃, 3-Cl-cyclopentyl 300 2,3-Cl₂-cyclopentyl 301 cyclohexyl 302 1-CH₃-cyclohexyl 303 2-CH₃-cyclohexyl 304 3-CH₃-cyclohexyl 305 2,3-(CH₃)₂-cyclohexyl 306 3,3-(CH₃)₂-cyclohexyl 307 1-Cl-cyclohexyl 308 2-Cl-cyclohexyl 309 3-Cl-cyclohexyl 310 2-CH₃, 3-Cl-cyclohexyl 311 2,3-Cl₂-cyclohexyl 312 CH₂—C≡C—H 313 CH₂—C≡C—Cl 314 CH₂—C≡C—Br 315 CH₂—C≡C-J 316 CH₂—C≡C—CH₃ 317 CH₂—C≡C—CH₂CH₃ 318 CH₂CH₂—C≡C—H 319 CH₂CH₂—C≡C—Cl 320 CH₂CH₂—C≡C—Br 321 CH₂CH₂—C≡C-J 322 CH₂CH₂—C≡C—CH₃ 323 CH₂CH₂CH₂—C≡C—H 324 CH₂CH₂CH₂—C≡C—Cl 325 CH₂CH₂CH₂—C≡C—Br 326 CH₂CH₂CH₂—C≡C-J 327 CH₂CH₂CH₂—C≡C—CH₃ 328 CH(CH₃)—C≡C—H 329 CH(CH₃)—C≡C—Cl 330 CH(CH₃)—C≡C—Br 331 CH(CH₃)—C≡C-J 332 CH(CH₃)—C≡C—CH₃ 333 —C≡C-[4-F—C₆H₄] 334 n-heptyl 335 n-octyl 336 vinyl 337 1-methylvinyl 338 2-methylvinyl 339 allyl 340 2-methylallyl 341 2-ethylallyl 342 1-methylallyl 343 1-ethylallyl, 344 1-methyl-2-butenyl 345 1-ethyl-2-butenyl 346 1-isopropyl-2-butenyl 347 1-n-butyl-2-butenyl 348 1-methyl-2-pentyl 349 1,4-dimethyl-2-pentenyl 350 propargyl 351 2-butynyl 352 3-butynyl 353 2-cyclopentenyl 354 1-cyclopentenyl 355 1-cyclohexenyl 356 2-cyclohexenyl 357 —CH₂F 358 —CHF₂ 359 —CF₃ 360 —CH₂—CHF₂ 361 —CH₂—CF₃ 362 —CHF—CF₃ 363 —CF₂—CHF₂ 364 —CF₂—CF₃ 365 CH₂—CF₂—CHF₂ 366 CH₂—CF₂—CF₃ 367 CF₂—CF₂—CF₃ 368 —CF₂—CHF—CF₃ 369 —CH₂(CF₂)₂—CF₃ 370 —CF₂(CF₂)₂—CF₃ 371 —CH₂(CF₂)₃—CF₃ 372 —CF₂(CF₂)₃—CF₃ 373 —CF₂—CF₂Omethyl 374 —CF₂—CF₂Oethyl 375 CF₂—CF₂O-n-propyl 376 CF₂—CF₂O-n-butyl 377 —CF₂—(CF₂)₂Omethyl 378 —CF₂—(CF₂)₂Oethyl 379 —CF₂—(CF₂)₂O-n-propyl 380 —CF₂—(CF₂)₂O-n-butyl 381 —(CF₂)₂—O—(CF₂)₂Omethyl 382 —(CF₂)₂—O—(CF₂)₂Oethyl 383 —(CF₂)₂—O—(CF₂)₂O-n-propyl 384 —(CF₂)₂—O—(CF₂)₂O-n-butyl 385 —CH₂—CHCl₂ 386 —CH₂—CCl₃ 387 —CCl₂—CHCl₂ 388 —CH₂CFCl₂ 389 —CH₂—CClF₂ 390 —CH₂—CCl₂—CCl₃ 391 —CH₂—CF₂—CHF—CF₂—CClF₂

Table 1:

Compounds of the formula Ia

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 2:

Compounds of the formula Ia in which X is O and R³ has one of the meanings given in table A.

Table 3:

Compounds of the formula Ib

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 4:

Compounds of the formula Ib in which X is O and R³ has one of the meanings given in table A.

Table 5:

Compounds of the formula IIa

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 6:

Compounds of the formula IIa in which X is O and R³has one of the meanings given in table A.

Table 7:

Compounds of the formula IIb

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 8:

Compounds of the formula IIb in which X is O and R³ has one of the meanings given in table A.

Table 9:

Compounds of the formula IIIa

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 10:

Compounds of the formula IIIa in which X is O and R³ has one of the meanings given in table A.

Table 11:

Compounds of the formula IIIb

in which X is a direct bond and R³ has one of the meanings given in table A.

Table 12:

Compounds of the formula IIIb, in which X is O and R³ has one of the meanings given in table A.

Table 13:

Compounds of the formula Ic

in which

R¹ is H, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 14:

Compounds of the formula Ic in which

R¹ is H, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 15:

Compounds of the formula Ic in which

R¹ is H, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 16:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 17:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 18:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 19:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 20:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 21:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 22:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 23:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 24:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 25:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 26:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in

Table 27:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 28:

Compounds of the formula Ic in which

R¹ is H, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 29:

Compounds of the formula Ic in which

R¹ is H, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 30:

Compounds of the formula Ic in which

R¹ is H, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 31:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 32:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 33:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 34:

Compounds of the formula Ic in which

R¹ is methyl, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 35:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 36:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 37:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 38:

Compounds of the formula Ic in which

R¹ is fluorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 39:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 40:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 41:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 42:

Compounds of the formula Ic in which

R¹ is chlorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 43:

Compounds of the formula IIc

in which

R¹ is H, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 44:

Compounds of the formula IIc in which

R¹ is H, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 45:

Compounds of the formula IIc in which

R¹ is H, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 46:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 47:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 48:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 49:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 50:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 51:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 52:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 53:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 54:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 55:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 56:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 57:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 58:

Compounds of the formula IIc in which

R¹ is H, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 59:

Compounds of the formula IIc in which

R¹ is H, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 60:

Compounds of the formula IIc in which

R¹ is H, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 61:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 62:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 63:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 64:

Compounds of the formula IIc in which

R¹ is methyl, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 65:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 66:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 67:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 68:

Compounds of the formula IIc in which

R¹ is fluorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 69:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 70:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 71:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 72:

Compounds of the formula IIc in which

R¹ is chlorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 73:

Compounds of the formula IIIc

in which

R¹ is H, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 74:

Compounds of the formula IIIc in which

R¹ is H, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 75:

Compounds of the formula IIIc in which

R¹ is H, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 76:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 77:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 78:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 79:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 80:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 81:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 82:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 83:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 84:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is H, X is a direct bond and R³ has one of the meanings given in table A.

Table 85:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 86:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is fluorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 87:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is chlorine, X is a direct bond and R³ has one of the meanings given in table A.

Table 88:

Compounds of the formula IIIc in which

R¹ is H, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 89:

Compounds of the formula IIIc in which

R¹ is H, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 90:

Compounds of the formula IIIc in which

R¹ is H, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 91:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 92:

Compounds of the formula IIIc in which

R¹ is methyl, R¹ is methyl, X is O and R³ has one of the meanings given in table A.

Table 93:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 94:

Compounds of the formula IIIc in which

R¹ is methyl, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 95:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 96:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 97:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 98:

Compounds of the formula IIIc in which

R¹ is fluorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 99:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is H, X is O and R³ has one of the meanings given in table A.

Table 100:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is methyl, X is O and R³ has one of the meanings given in table A.

Table 101:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is fluorine, X is O and R³ has one of the meanings given in table A.

Table 102:

Compounds of the formula IIIc in which

R¹ is chlorine, R^(1′) is chlorine, X is O and R³ has one of the meanings given in table A.

Table 103:

Compounds of the formula Id

in which R² is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 104:

Compounds of the formula Id in which

R² is OH, X is a direct bond and R³ has one of the meanings given-in table A.

Table 105:

Compounds of the formula Id in which

R² is methoxy, X is a direct bond and R³ has one of the meanings given in table A.

Table 106:

Compounds of the formula Id in which

R² is methyl, X is O and R³ has one of the meanings given in table A.

Table 107:

Compounds of the formula Id in which

R² is OH, X is O and R³ has one of the meanings given in table A.

Table 108:

Compounds of the formula Id in which

R² is methoxy, X is O and R³ has one of the meanings given in table A.

Table 109:

Compounds of the formula IId

in which R² is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 110:

Compounds of the formula IId in which

R² is OH, X is a direct bond and R³ has one of the meanings given in table A.

Table 111:

Compounds of the formula IId in which

R² is methoxy, X is a direct bond and R³ has one of the meanings given in table A.

Table 112:

Compounds of the formula IId in which

R² is methyl, X is O and R³ has one of the meanings given in table A.

Table 113:

Compounds of the formula IId in which

R² is OH, X is O and R³ has one of the meanings given in table A.

Table 114:

Compounds of the formula IId in which

R² is methoxy, X is O and R³ has one of the meanings given in table A.

Table 115:

Compounds of the formula IIId

in which R² is methyl, X is a direct bond and R³ has one of the meanings given in table A.

Table 116:

Compounds of the formula IIId in which

R² is OH, X is a direct bond and R³ has one of the meanings given in table A.

Table 117:

Compounds of the formula IIId in which

R² is methoxy, X is a direct bond and R³ has one of the meanings given in table A.

Table 118:

Compounds of the formula IIId in which

R² is methyl, X is O and R³ has one of the meanings given in table A.

Table 119:

Compounds of the formula IIId in which

R² is OH, X is O and R³ has one of the meanings given in table A.

Table 120:

Compounds of the formula IIId in which

R² is methoxy, X is O and R³ has one of the meanings given in table A.

General Synthesis

The active compounds I, II and III can be prepared by processes known from the literature by reacting activated trifluorothiophenecarboxylic acid derivatives IV with an aniline V [Houben-Weyl: “Methoden der organ. Chemie” [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart, N.Y. 1985, Volume E5, pp. 941-1045.]. Activated carboxylic acid derivatives are, for example, halides, activated esters, anhydrides, azides, for example chlorides, fluorides, bromides, para-nitrophenyl esters, pentafluorophenyl esters, N-hydroxysuccinimides, hydroxybenzotriazol-1-yl esters.

The active compounds I, II and III can be prepared by reacting the acids VI with an aniline V in the presence of a coupling agent.

Suitable coupling agents are, for example:

-   -   coupling agents based on carbodiimides, for example         N,N′-dicyclohexylcarbodiimide [J. C. Sheehan, G. P. Hess, J. Am.         Chem. Soc. 1955, 77, 1067],         N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide;     -   coupling agents which form mixed anhydrides with carbonic         esters, for example         2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline [B. Belleau, G.         Malek, J. Amer. Chem. Soc. 1968, 90,1651.],         2-isobutyloxy-1-isobutyloxycarbonyl-1,2-dihydroquinoline [Y.         Kiso, H. Yajima, J. Chem. Soc., Chem. Commun. 1972, 942.];     -   coupling agents composed of phosphonium base, for example         (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium         hexafluorophosphate [B. Castro, J. R. Domoy, G. Evin, C. Selve,         Tetrahedron Left. 1975, 14,1219.],         (benzotriazol-1-yl-oxy)tripyrrolidinophosphonium         hexafluorophosphate [J. Coste et al., Tetrahedron Lett. 1990,         31, 205.];     -   coupling agents based on uronium or having a guanidinium N-oxide         structure, for example         N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium         hexafluorophosphate [R. Knorr, A. Trzeciak, W. Bannwarth, D.         Gillessen, Tetrahedron Left. 1989, 30, 1927.],         N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uronium         tetrafluoroborate, (benzotriazol-1-yloxy)dipiperidinocarbenium         hexafluorophosphate [S. Chen, J. Xu, Tetrahedron Lett. 1992, 33,         647.];     -   coupling agents which form acid chlorides, for example         bis(2-oxo-oxazolidinyl)phosphinic chloride [J. Diago-Mesequer,         Synthesis 1980, 547.].

The active compounds I, II and III where R²=unsubstituted or halogen-substituted alkyl or unsubstituted or halogen-substituted cycloalkyl can be prepared by alkylation of the amides I, II or III (in which R²=hydrogen and which are obtainable by a) or b)) with suitable alkylating agents in the presence of bases:

The trifluoromethylthiophenecarboxylic acids VI can be prepared by methods known from the literature [M. Nishida et al., J. Fluorine Chem. 1990, 46, 445. JP 1980-5059135. DE 3620064. U.S. Pat. No. 4,803,205. W. Dmowski, K. Piasecka, J. Fluorine Chem. 1996, 78, 59.]

Employing these, the activated thiophenecarboxylic acid derivatives IV can be synthesized by methods known from the literature [Houben-Weyl: “Methoden der organ. Chemie”, Georg-Thieme-Verlag, Stuttgart, N.Y. 1985, Volume E5, pp. 587-614, 633-772.]

The anilines V can be synthesized by methods known from the literature [Houben-Weyl: “Methoden der organ. Chemie”, Georg-Thieme-Verlag, Stuttgart, N.Y., Volume XI, Part 1, pp. 9-1005.]

The compounds I, II and III are suitable for use as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some are systemically effective and they can be used in plant protection as foliar and soil fungicides.

They are particularly important in the control of a multitude of fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugar cane, vines, fruits and ornamental plants, and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

They are especially suitable for controlling the following plant diseases:

-   -   Alternaria species on fruit and vegetables,     -   Botrytis cinerea (gray mold) on strawberries, vegetables,         ornamental plants and grapevines,     -   Cercospora arachidicola on groundnuts,     -   Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,     -   Erysiphe graminis (powdery mildew) on cereals,     -   Fusarium and Verticillium species on various plants,     -   Helminthosporium species on cereals,     -   Mycosphaerella species on bananas and groundnuts,     -   Phytophthora infestans on potatoes and tomatoes,     -   Plasmopara viticola on grapevines,     -   Podosphaera leucotricha on apples,     -   Pseudocercosporella herpotrichoides on wheat and barley,     -   Pseudoperonospora species on hops and cucumbers,     -   Puccinia species on cereals,     -   Pyricularia oryzae on rice,     -   Rhizoctonia species on cotton, rice and lawns,     -   Septoria nodorum on wheat,     -   Sphaerotheca fuliginea (mildew of cucumber) on cucumbers,     -   Uncinula necator on grapevines,     -   Ustilago species on cereals and sugar cane,     -   Venturia species (scab) on apples and pears,     -   Septoria tritici,     -   Pyrenophora species,     -   Leptosphaeria nodorum,     -   Rhynchosporium species and     -   Typhula species.

The compounds I, II and III are also suitable for controlling harmful fungi, such as Paecilomyces varioti, in the protection of materials (e.g. wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.

The compounds I, II and III are employed by treating the fungi or the plants, seeds, materials or soil to be protected from fungal attack with a fungicidally effective amount of the active compounds. The application can be carried out both before and after the infection of the materials, plants or seeds by the fungi.

The fungicidal compositions generally comprise between 0.1 and 95%, preferably between 0.5 and 90%, by weight of active compound.

When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha.

In seed treatment, amounts of active compound of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kilogram of seed are generally necessary.

When used in the protection of materials or stored products, the amount of active compound applied depends on the kind of application area and on the effect desired. Amounts customarily applied in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material.

The compounds I, II and III can be converted to the usual formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the respective use intended; it should in any case guarantee a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known way, e.g. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it being possible, when water is the diluent, also to use other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are essentially: solvents, such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic ores (e.g. highly dispersed silicic acid, silicates); emulsifiers, such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants, such as lignosulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid and dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids, and alkali metal and alkaline earth metal salts thereof, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol and nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Petroleum fractions having medium to high boiling points, such as kerosene or diesel oil, furthermore coal tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene or isophorone, or highly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water, are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.

Powders, compositions for broadcasting and dusts can be prepared by mixing or mutually grinding the active substances with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are, e.g., mineral earths, such as silica gels, silicic acids, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate or ureas, and plant products, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

The formulations generally comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active compound. The active compounds are employed therein in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples for formulations are:

-   I. 5 parts by weight of a compound according to the invention are     intimately mixed with 95 parts by weight of finely divided kaolin.     In this way, a dust comprising 5% by weight of the active compound     is obtained. -   II. 30 parts by weight of a compound according to the invention are     intimately mixed with a mixture of 92 parts by weight of pulverulent     silica gel and 8 parts by weight of liquid paraffin, which had been     sprayed onto the surface of this silica gel. In this way, an active     compound preparation with good adhesive properties (active compound     content 23% by weight) is obtained. -   III. 10 parts by weight of a compound according to the invention are     dissolved in a mixture consisting of 90 parts by weight of xylene, 6     parts by weight of the addition product of 8 to 10 mol of ethylene     oxide with 1 mol of the N-mono-ethanolamide of oleic acid, 2 parts     by weight of the calcium salt of dodecyl-benzenesulfonic acid and 2     parts by weight of the addition product of 40 mol of ethylene oxide     with 1 mol of castor oil (active compound content 9% by weight). -   IV. 20 parts by weight of a compound according to the invention are     dissolved in a mixture consisting of 60 parts by weight of     cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight     of the addition product of 7 mol of ethylene oxide with 1 mol of     isooctylphenol and 5 parts by weight of the addition product of 40     mol of ethylene oxide with 1 mol of castor oil (active compound     content 16% by weight). -   V. 80 parts by weight of a compound according to the invention are     intimately mixed with 3 parts by weight of the sodium salt of     diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the     sodium salt of a lignosulfonic acid from a sulfite waste liquor and     7 parts by weight of pulverulent silica gel and are ground in a     hammer mill (active compound content 80% by weight). -   VI. 90 parts by weight of a compound according to the invention are     mixed with 10 parts by weight of N-methyl-a-pyrrolidone and a     solution is obtained which is suitable for use in the form of very     small drops (active compound content 90% by weight). -   VII. 20 parts by weight of a compound according to the invention are     dissolved in a mixture consisting of 40 parts by weight of     cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight     of the addition product of 7 mol of ethylene oxide with 1 mol of     isooctylphenol and 10 parts by weight of the addition product of 40     mol of ethylene oxide with 1 mol of castor oil. By running the     solution into 100 000 parts by weight of water and finely dispersing     it therein, an aqueous dispersion is obtained comprising 0.02% by     weight of the active compound. -   VIII. 20 parts by weight of a compound according to the invention     are intimately mixed with 3 parts by weight of the sodium salt of     diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the     sodium salt of a lignosulfonic acid from a sulfite waste liquor and     60 parts by weight of pulverulent silica gel and are ground in a     hammer mill. A spray emulsion comprising 0.1% by weight of the     active compound is obtained by fine dispersion of the mixture in 20     000 parts by weight of water. -   IX. 10 parts by weight of the compound according to the invention     are dissolved in 63 parts by weight of cyclohexanone, 27 parts by     weight of dispersing agent (for example a mixture of 50 parts by     weight of the adduct of 7 mol of ethylene oxide to 1 mol of     isooctylphenol and 50 parts by weight of the adduct of 40 mol of     ethylene oxide to 1 mol of castor oil). The stock solution is then     diluted to the desired concentration, for example a concentration in     the range from 1 to 100 ppm, by distribution in water.

The active compounds can be used as such, in the form of their formulations or of the application forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, compositions for broadcasting or granules, by spraying, atomizing, dusting, broadcasting or watering. The application forms depend entirely on the intended uses; they should in any case guarantee the finest possible dispersion of the active compounds according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water, as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which concentrates are suitable for dilution with water.

The concentrations of active compound in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are between 0.0001 and 10%. Often even small amounts of active compound I are sufficient in the ready-to-use preparation, for example 2 to 200 ppm. Ready-to-use preparations with concentrations of active compound in the range from 0.01 to 1% are also preferred.

The active compounds can also be used with great success in the ultra low volume (ULV) process, it being possible to apply formulations with more than 95% by weight of active compound or even the active compound without additives.

Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if need be also not until immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1:10 to 10:1.

The compositions according to the invention can, in the application form as fungicides, also be present together with other active compounds, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. On mixing the compounds I or the compositions comprising them in the application form as fungicides with other fungicides, in many cases an expansion of the fungicidal spectrum of activity is obtained.

The following list of fungicides, with which the compounds according to the invention can be used in conjunction, is intended to illustrate the possible combinations but does not limit them:

-   -   sulfur, dithiocarbamates and their derivatives, such as         iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate,         zinc ethylenebisdithiocarbamate, manganese         ethylenebisdithiocarbamate, manganese zinc         ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide,         ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),         ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc         (N,N′-propylenebisdithiocarbamate) or         N,N′-polypropylenebis(thiocarbamoyl)disulfide;     -   nitro derivatives, such as dinitro(1-methylheptyl)phenyl         crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,         2-sec-butyl4,6-dinitrophenyl isopropyl carbonate or diisopropyl         5-nitroisophthalate;     -   heterocyclic substances, such as 2-heptadecyl-2-imidazoline         acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine,         O,O-diethyl phthalimidophosphonothioate,         5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,         2,3-dicyano-1,4-dithioanthraquinone,         2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl         1-(butylcarbamoyl)-2-benzimidazolecarbamate,         2-(methoxycarbonylamino)benzimidazole, 2-(2-furyl)benzimidazole,         2-(4-thiazolyl)benzimidazole,         N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,         N-(trichloromethylthio)tetrahydrophthalimide or         N-(trichloromethylthio)phthalimide,     -   N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfamide,         5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,         2-thiocyanatomethylthiobenzothiazole,         1,4-dichloro-2,5-dimethoxybenzene,         4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,         2-thiopyridine 1-oxide, 8-hydroxyquinoline or its copper salt,         2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,         2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin 4,4-dioxide,         2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,         2-methylfuran-3-carboxanilide,         2,5-dimethylfuran-3-carboxanilide,         2,4,5-trimethyl-furan-3-carboxanilide,         N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,         N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,         2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine         2,2,2-trichloroethyl acetal,         piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide,         1-(3,4-dichloroanilino)-1-formyl-amino-2,2,2-trichloroethane,         2,6-dimethyl-N-tridecylmorpholine or its salts,         2,6-dimethyl-N-cyclododecylmorpholine or its salts,         N-[3-(p-(tert-butyl)phenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,         N-[3-(p-(tert-butyl)phenyl)-2-methyl-propyl]piperidine,         1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,         1-[2-(2,4-dichlorophenyl)-4-(n-propyl)-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,         N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea,         1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,         1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,         (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole,         a-(2-chlorophenyl)-a-(4-chlorophenyl)-5-pyrimidine methanol,         5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,         bis(p-chlorophenyl)-3-pyridinemethanol,         1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene or         1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,     -   strobilurins, such as methyl         E-methoxyimino[a-(o-tolyloxy)-o-tolyl]acetate, methyl         E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,         methyl E-methoxyimino[a-(2-phenoxyphenyl)]acetamide, methyl         E-methoxyimino-[a-(2,5-dimethylphenoxy)-o-tolyl]acetamide,     -   anilinopyrimidines, such as         N-(4,6-dimethylpyrimidin-2-yl)aniline,         N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline or         N-[4-methyl-6-cyclopropylpyrimidin-2-yl]-aniline,     -   phenylpyrroles, such as         4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,     -   cinnamamides, such as         3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl-morpholine,     -   and various fungicides, such as dodecylguanidine acetate,         3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,         hexachlorobenzene, methyl         N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate,         N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-DL-alanine methyl         ester,         N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,         N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alanine methyl ester,         5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,         3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,         3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,         N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,         2-cyano-N-(ethylaminocarbonyl)-2-[methoxyimino]acetamide,         1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,         2,4-difluoro-a-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,         N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,         1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

Preparation Examples:

-   a) Synthesis of     N-(3-isopropoxyphenyl)-2-trifluoromethylthiophene-3-carboxamide:     12.9 g of 2-trifluoromethylthiophene-3-carboxylic acid are dissolved     in 78 g of thionyl chloride, and the reaction mixture is heated     under reflux for 2 h. The mixture is then concentrated under reduced     pressure, giving 13.5 g of 2-trifluoromethylthiophene-3-carbonyl     chloride. 1.0 g of this is added dropwise to a solution of 0.7 g of     meta-isopropoxyaniline and 1.4 g of triethylamine in 35 ml of     dichloromethane. The mixture is stirred at room temperature for     15 h. The mixture is then washed once with in each case 20 ml of 2%     strength hydrochloric acid and saturated NaHCO₃ solution, and the     organic phase is dried over magnesium sulfate and concentrated under     reduced pressure. Chromatographic purification using a mixture of     methyl tert-butyl ether and cyclohexane gives 1.15 g of the product.     M.p.=58-60° C. -   b) Synthesis of     N-(2-(2,2,2-trifluoroethoxy)phenyl)-3-trifluoromethylthiophene-2-carboxamide:     -   0.39 g of 3-trifluoromethylthiophene-2-carboxylic acid, 0.36 g         of 2-(2,2,2-trifluoroethoxy)aniline, 0.53 g of         bis(2-oxo-3-oxazolidinyl)phosphinic chloride and 0.29 g of         triethylamine are dissolved in 20 ml of dichloromethane. The         mixture is stirred at room temperature for 15 h. 60 ml of methyl         tert-butyl ether are then added, the mixture is washed in each         case once with 5% strength hydrochloric acid, 5% strength         aqueous sodium hydroxide solution and water and the organic         phase is dried with magnesium sulfate and concentrated under         reduced pressure. Chromatographic purification using a mixture         of methyl tert-butyl ether and toluene gives 0.56 g of the         product. M.p.=125-127° C. -   c) Synthesis of     N-(3-isopropoxyphenyl)-3-trifluoromethylthiophene-4-carboxamide:     0.30 g of 3-trifluoromethylthiophene-4-carboxylic acid, 0.23 g of     3-isopropyl-oxyaniline and 0.31 g of triethylamine and 0.43 g of     bis(2-oxo-3-oxazolidinyl)-phosphinic chloride are dissolved in 30 ml     of dichloromethane at 0° C. The mixture is stirred at 0° C. for 15 h     and then at room temperature for 7 h. 60 ml of methyl tert-butyl     ether are then added, the mixture is washed in each case once with     5% strength hydrochloric acid, 5% strength sodium bicarbonate     solution and water and the organic phase is dried over magnesium     sulfate and concentrated under reduced pressure. Chromatographic     purification using a mixture of methyl tert-butyl ether and toluene     gives 0.4 g of the product as an oil.

The compounds listed in tables 121, 122 and 123 are prepared analogously to the synthesis examples described above. a) 3-Trifluoromethylthiophene-2-carboxanilides

TABLE 121 I

m.p./ No. R Pos. R R¹ consistency Spectroscopic data I-1 ortho sec-butyl H 69-70° C. I-2 ortho cyclopentyl H 139-141° C. I-3 ortho cyclohexyl H 100-101° C. I-4 ortho n-pentyl H 88-89° C. I-5 ortho 1,1,2,2- H 59-61° C. tetrafluoroethoxy I-6 ortho para-chlorophenyl H 148-150° C. I-7 ortho para-fluorophenyl H 121-122° C. I-8 meta isopropyloxy H 58-60° C. I-9 meta 1,1,2,2- H resin IR[cm⁻¹]: 1659, 1609, tetrafluoroethoxy 1552, 1491, 1443, 1397, 1292, 1252, 1197, 1126, 909, 797, 768, 725, 680. I-10 meta n-hexyloxy H 73-74° C. I-11 meta cyclopentyloxy H resin IR[cm⁻¹]: 2961, 1657, 1610, 1599, 1553, 1491, 1442, 1396, 1290, 1257, 1156, 1130, 908, 770, 725. I-12 ortho phenyl H 113-115° C. I-13 ortho para-isopropylphenyl H 125-126° C. I-14 ortho 2,2,2-trifluoroethoxy H 125-127° C. I-15 ortho 2,2,3,3,3- H 56-58° C. pentafluoropropyloxy 1-16 ortho 2,2,3,3,4,4,5,5,6,6,7,7,7- H IR[cm⁻¹]: 1687, 1608, tridecafluoroheptyl- 1545, 1526, 1454, 1293, oxy 1241, 1207, 1145, 1128, 748. I-17 ortho sec-butyl methyl resin 7.75(m, 1H); 7.67 (s(broad), 1H): 7.18-7.29 (m, 4H); 6.99(s; 1H); 2.76- 2.85(m, 1H); 2.53(s, 3H); 1.51-1.69(m, 2H); 1.24(d, 3H); 0.86(t, 3H). I-18 ortho para-chlorophenyl methyl 69-72° C. I-19 meta isopropyloxy methyl 93-96° C. I-20 ortho 1,1,2,2-tetra- methyl 59-62° C. fluoroethoxy Pos. R = position of R substituent relative to N—H group m.p. = melting point

b) 2-Trifluoromethylthiophene-3-carboxanifides

TABLE 122 II

Pos. m.p./ No. R R consistency Spectroscopic data II-1 ortho sec-butyl 92-93° C. II-2 ortho cyclopentyl 161-163° C. II-3 ortho cyclohexyl 101-103° C. II-4 ortho n-pentyl 100-102° C. II-5 ortho 1,1,2,2-tetra- 78-79° C. fluoroethoxy II-6 ortho para- 152-153° C. chlorophenyl II-7 ortho para-  99-101° C. fluorophenyl II-8 meta isopropyloxy resin IR[cm⁻¹]: 2978, 1659, 1611, 1599, 1555, 1492, 1431, 1296, 1259, 1201, 1133, 1021, 1005, 688. II-9 meta 1,1,2,2-tetra- resin IR[cm⁻¹]: 1662, 1609, 1555, fluoroethoxy 1491, 1432, 1298, 1254, 1195, 1130, 1022, 852, 796, 760, 721, 684. II-10 meta n-hexyloxy resin IR[cm⁻¹]: 2955, 2932, 1659, 1611, 1600, 1555, 1494, 1469, 1432, 1295, 1259, 1200, 1178, 1133, 1021. Pos. R = position of R substituent relative to N—H group m.p. = melting point

c) 3-Trifluoromethylthiophene-4-carboxanilides

TABLE 123 III

Pos. m.p./ No. R R consistency Spectroscopic data III-1 ortho para-chlorophenyl 130-134° C. III-2 meta isopropyloxy oil 1H NMR(CDCl₃), δ [ppm]: 1.30(d, 6H); 4.53(q, 1H); 6.70(m, 1H); 7.05 (m, 1H); 7.25(m, 1H); 7.30(m, 1H); 7.70(s, 1H); 7.80(m, 1H); 7.88(m, 1H). III-3 ortho para-fluorophenyl 120-122° .C III-4 ortho ortho-methylphenyl 86-87° C. III-5 ortho sec-butyl  99-100° C. III-6 ortho n-pentyl 106-108° C. III-7 ortho cyclopentyl 110-113° C. III-8 ortho cyclohexyl 142-143° C. III-9 ortho 1,1,2,2- 85°87° C. tetrafluoroethoxy III-10 ortho 2,2,3,3- 81-82° C. tetrafluoropropyloxy III-11 ortho 2,2,3,3,3- 90-92° C. pentafluoropropyloxy III-12 meta cyclopentyloxy 82-84° C. III-13 meta 1,1,2,2- 78-83° C. tetrafluoroethoxy III-14 ortho phenyl 82-85° C. III-15 ortho 2,2,3-trifluoroethoxy 93-97° C. III-16 ortho para-(isopropyl)- 79-83° C. phenyl Pos. R = position of R substituent relative to N—H group m.p. = melting point

USE EXAMPLE 1

Activity and Persistency against Gray Mold, Caused by Botrytis cinerea, on Bell-pepper Leaves

Bell-pepper seedlings of the cultivar “Neusiedler Ideal Elite” having 4-5 well-developed leaves were sprayed to runoff point with an aqueous suspension having the concentration stated below of active compounds. The suspension or emulsion was prepared from a stock solution containing 10% of active compound in a mixture comprising 85% of cyclohexanone and 5% of emulsifier. The plants were then cultivated for a further 7 days, and the treated plants were then inoculated with a spore suspension of Botrytis cinerea, which comprised 1.7×10⁶ spores/ml in a 2% strength aqueous biomalt solution. The test plants were then placed in a climatized chamber at 22-24° C. in high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %, giving not only an indication of the fungicidal action of the substances but also of the persistency.

Number Foliar infection [%] at 63 ppm I-1 5 I-2 7 I-3 3 I-5 3 I-6 1 I-7 1 I-8 10 I-11 7 II-2 10 II-3 5 II-5 3 II-7 1 II-8 5 II-10 10 Untreated 90

USE EXAMPLE 2

Protective Activity against Gray Mold, Caused by Botrytis cinerea, on Bell-pepper Leaves

Bell-pepper seedlings of the cultivar “Neusiedler Ideal Elite” having 4-5 well-developed leaves were sprayed to runoff point with an aqueous suspension having the concentration stated below of active compounds. The active compounds were separately prepared as a stock solution containing 0.25% by weight of active compound in acetone or dimethyl sulfoxide. This solution was admixed with 1% by weight of Emulgator Uniperol® EL (wetting agent based on ethoxylated alkylphenols which has an emulsifying and dispersing effect) and diluted with water to the desired concentration. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea, comprising 1.7×10⁶ spores/ml in a 2% strength aqueous biomalt solution. The test plants were then placed in a climatized chamber at 22-24° C. in high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %.

Number Foliar infection [%] at 250 ppm III-4 3 III-5 3 III-7 7 Untreated 100

USE EXAMPLE 3

Protective Activity Against Mildew of Cucumber Caused by Sphaerotheca fuliginea

Leaves of potted cucumber seedlings of the cultivar “Chinese Snake”, in the cotyledon stage, were sprayed to runoff point with an aqueous suspension having the concentration stated below of active compounds. The suspension or emulsion was prepared from a stock solution containing 10% of active compound in a mixture comprising 85% of cyclohexanone and 5% of emulsifier. 20 hours after the spray coating had dried on, the plants were inoculated with an aqueous spore suspension of mildew of cucumber (Sphaerotheca fuliginea). The plants were then cultivated in a greenhouse at 20-24° C. and 60-80% relative atmospheric humidity for 7 days. The extent of mildew development was then determined visually in % infection of the cotyledon area.

Number Foliar infection [%] at 63 ppm I-3 5 I-5 5 I-6 0 I-7 0 I-12 0 I-13 0 II-3 3 II-6 0 II-7 5 Untreated 90 

1. A trifluoromethylthiophenecarboxanilide of the formulae I, II and III

in which the substituents are as defined below: R¹, R⁴ independently of one another are C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy (it being possible for these groups to be substituted by halogen), H, halogen, nitro, CN; R² is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy (it being possible for these groups to be substituted by halogen), H, OH; R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl, C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl, C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl (it being possible for these groups to be substituted by R⁷); phenyl, phenyl-C₁-C₆-alkyl, phenyl-C₂-C₆-alkenyl, phenyl-C₂-C₆-alkynyl, phenyloxy-C₁-C₆-alkyl, phenyloxy-C₂-C₆-alkenyl, phenyloxy-C₂-C₆-alkynyl, where the alkyl, alkenyl and alkynyl moiety may be substituted by R⁷ and the phenyl ring may be substituted by R⁵; —C(R⁸)═NOR⁶; X is O, S or a direct bond; R⁵ is H, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl (it being possible for these groups to be substituted by halogen), halogen, nitro, CN, phenyl (which may be substituted by R¹), phenoxy (which may be substituted by R¹), C₁-C₆-alkylphenyl, where the alkyl moiety may be substituted by halogen and the phenyl ring may be substituted by R¹; R⁶ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl (it being possible for these groups to be substituted by halogen), phenyl, which may be substituted by R¹; R⁷ is C₁-C₄-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₂-C₈-alkynyloxy, C₁-C₄-alkoxy-C₁-C₈-alkoxy (it being possible for these groups to be substituted by halogen), halogen; R⁸ is H, R⁷ or C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl, C₅-C₁₂-cycloalkenyl, C₃-C₁₂-cycloalkyl-C₁-C₄-alkyl (it being possible for these groups to be substituted by halogen); phenyl, which may be substituted by R⁵; n is 0-4; m is 0,
 1. 2. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim 1 in which R¹ is H, halogen or C₁-C₄alkyl, which may be substituted by halogen.
 3. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim 2 in which R¹ is fluorine, chlorine, bromine or methyl.
 4. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to any of claims 1 to 3 in which R² is H, methyl, OH or methoxy.
 5. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim 1 in which R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl, C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl, it being possible for these groups to be substituted by halogen and C₁-C₄-alkyl; phenyl, phenyl-C₁-C₆-alkyl, it being possible for the phenyl ring to be substituted by R⁵; or —C(C₁-C₄-alkyl)=NO—R⁶, it being possible for the C₁-C₄-alkyl group to be substituted by halogen.
 6. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim 1 in which R⁴ is C₁-C₄-alkyl, C₁-C₄-alkoxy (it being possible for these groups to be substituted by halogen) or halogen.
 7. A trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim 1 in which X is a direct bond or O.
 8. A trifluoromethylthiophenecarboxanilide of the formulae Ia, Ib, IIa, IIb, IIIa and IIIb according to claim 1

in which the substituents are as defined below: R³ is C₁-C₁₂-alkyl, C₃-C₁₂-cycloalkyl, C₂-C₁₂-alkenyl, C₅-C₁₂-cycloalkenyl, C₂-C₁₂-alkynyl, it being possible for these groups to be substituted by halogen or C₁-C₄-alkyl; phenyl, phenyl-C₁-C₆-alkyl, it being possible for the phenyl ring to be substituted by R⁵, or —C(C₁-C₄-alkyl)=NO—R⁶, it being possible for the C₁-C₄-alkyl group to be substituted by halogen; X is a direct bond or O.
 9. A trifluoromethylthiophenecarboxanilide of the formulae Ia, Ib, IIa, IIb, IIIa and IIIb according to claim 8 in which X is a direct bond.
 10. A trifluoromethylthiophenecarboxanilide of the formulae Ia, Ib, IIa, IIb, IIIa and IIIb according to claim 8 in which X is oxygen.
 11. A method of controlling harmful fungi, wherein the harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them are treated with the trifluoromethylthiophenecarboxanilides of the formula Ia, Ib, IIa, IIb, IIIa or IIIb according to claim
 8. 12. A fungicidal composition comprising a fungicidally effective amount of at least one trifluoromethylthiophenecarboxanilide of the formula I, II or III according to claim
 1. 13. A method of controlling harmful fungi, wherein the harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them are treated with a fungicidal composition according to claim 12 comprising at least a fungicidally effective amount of a trifluoromethylthiophenecarboxanilide of the formula I, II or III. 